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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O6
Molecular Weight 300.2629
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSMETIN

SMILES

COC1=CC=C(C=C1O)C2=CC(=O)C3=C(O2)C=C(O)C=C3O

InChI

InChIKey=MBNGWHIJMBWFHU-UHFFFAOYSA-N
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

HIDE SMILES / InChI

Molecular Formula C16H12O6
Molecular Weight 300.2629
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Diosmetin is the aglycone of the flavonoid glycoside diosmin, which occurs naturally in citrus fruits. Diosmetin is found in the legume Acacia farnesiana Wild and Olea europaea L. leaves. Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflammatory activities. Diosmetin increased inhibitory GSK-3beta phosphorylation, while selectively reducing gamma-secretase activity, Abetta generation, tau hyperphosphorylation and pro-inflammatory activation of microglia in vitro, without altering Notch processing. Therefore, diosmetin could be considered as potential candidate for novel anti- Alzheimer's disease therapy. Diosmetin is ER-beta agonist and potential novel drug for the acute myeloid leukemia treatment.

Originator

Sources: DOI: 10.1002/hlca.19250080179

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A benzoquinone and flavonoids from Cyperus alopecuroides.
2002 Jun
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.
2003 May
A validated HPLC determination of the flavone aglycone diosmetin in human plasma.
2004 Dec
Antitubercular constituents of Valeriana laxiflora.
2004 Jun
[Investigation of the hepatoprotector action of natural flavonoids].
2004 Nov-Dec
Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones.
2005 Aug
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.
2005 Feb 15
In vitro antioxidant activity of some Teucrium species (Lamiaceae).
2005 Jun
Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece.
2006 Jul 26
Anti-proliferative and antioxidant constituents from Tecoma stans.
2006 Nov-Dec
Raddeanalin, a new flavonoid glycoside from the leaves of Salix raddeana Laksh.
2007 Apr-Aug
Complete assignments of NMR data of 13 hydroxymethoxyflavones.
2007 Dec
Pensteminoside, an unusual catalpol-type iridoid from Penstemon gentianoides HBK (Plantaginaceae).
2007 Jul
Two new flavonoids from Origanum vulgare.
2008
Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages.
2008 Apr
Effect of flavonoids on rat splenocytes, a structure-activity relationship study.
2008 Aug 15
Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation.
2008 Feb
Flavonoids from Galium verum L.
2008 Jul-Aug
New features on the fragmentation and differentiation of C-glycosidic flavone isomers by positive electrospray ionization and triple quadrupole mass spectrometry.
2008 Jun
Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway.
2008 Jun
Camptothecinoids from the seeds of Taiwanese Nothapodytes foetida.
2008 Jun 16
[Studies on chemical constituents in Huangjuhua (flowers of Chrysanthemum morifolium)].
2008 Mar
A new ferulic acid ester and other constituents from Dracocephalum peregrinum.
2008 Oct
Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana.
2009 Feb
Simultaneous determination of the flavonoid aglycones diosmetin and hesperetin in human plasma and urine by a validated GC/MS method: in vivo metabolic reduction of diosmetin to hesperetin.
2009 Feb
Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450.
2009 Feb 8
Stimulatory constituents of Eclipta prostrata on mouse osteoblast differentiation.
2009 Jan
Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation.
2009 Jul
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.
2009 Jun 16
The phytochemical analysis and antioxidant activity assessment of orange peel (Citrus sinensis) cultivated in Greece-Crete indicates a new commercial source of hesperidin.
2009 Mar
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.
2009 Mar 25
[Studies on flavones from Flos Chrysanthemi Indici].
2009 Oct
Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells.
2009 Sep
[Chemical constituents of Lobelia chinensis].
2009 Sep
Effects of Various Flavonoids on the α-Synuclein Fibrillation Process.
2010 Jan 28
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.
2010 Jun
Simultaneous determination of diosmin and diosmetin in human plasma by ion trap liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: Application to a clinical pharmacokinetic study.
2010 Mar 11
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.
2010 Mar 2
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.
2011 May 1
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.
2015 Mar
Patents

Sample Use Guides

Mice: 50mg /kg/every other day for 6 weeks
Route of Administration: Intraperitoneal
Diosmetin caused G1 arrest at 10 microM in MDA-MB 468 cells after 48-h treatment whereas this effect was not observed in MCF-10A cells.
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:52:49 UTC 2023
Edited
by admin
on Thu Jul 06 00:52:49 UTC 2023
Record UNII
TWZ37241OT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIOSMETIN
INCI   MI   WHO-DD  
INCI  
Official Name English
4'-METHYLLUTEOLIN
Common Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-
Systematic Name English
3',5,7-TRIHYDROXY-4'-METHOXYFLAVONE
Systematic Name English
DIOSMETIN [INCI]
Common Name English
DIOSMETIN [MI]
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)CHROMEN-4-ONE
Systematic Name English
DIOSMETINE
Common Name English
LUTEOLIN-4'-METHYL ETHER
Common Name English
CYANIDENON-4'-METHYL ETHER 1479
Common Name English
DIOSMETOL
Common Name English
Diosmetin [WHO-DD]
Common Name English
5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
FLAVONE, 3',5,7-TRIHYDROXY-4'-METHOXY-
Systematic Name English
Classification Tree Code System Code
DSLD 4156 (Number of products:7)
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
Code System Code Type Description
EVMPD
SUB35834
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
HSDB
8101
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
WIKIPEDIA
DIOSMETIN
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID80199966
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
DAILYMED
TWZ37241OT
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
SMS_ID
100000128590
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
PUBCHEM
5281612
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
CHEBI
4630
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
RXCUI
1314347
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY RxNorm
CAS
520-34-3
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
FDA UNII
TWZ37241OT
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
DRUG CENTRAL
4601
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-291-8
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
MERCK INDEX
M4594
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY Merck Index
MESH
C039602
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
DRUG BANK
DB11259
Created by admin on Thu Jul 06 00:52:50 UTC 2023 , Edited by admin on Thu Jul 06 00:52:50 UTC 2023
PRIMARY
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